Why boring work is inevitable

What's up, everyone? This is Alex, the host of Founders Journal. As you may know, I built Morning Brew from my senior year of college until we sold the business in 2020. And now I'm building a variety of businesses in different spaces and different stages. I'm basically averaging 1 to 2 new businesses per year, and because of that, I have had the opportunity to test a ton of different products and services, ultimately landing on a core software stack that serves as my business operating system whenever I start a new company. I have my go-to banking service. I have my go-to formation service. I have my go-to domain hosting service. But probably the most important of them all is my HR service, Gusto. If you're a longtime Founders Journal listener, you know how much I think about people in the context of business. A business is nothing without its people, which means a platform that helps me manage and take care of my people is invaluable. And that means I've tried every HR platform under the sun, always with the same exact goals in mind. First, I want a product that's intuitive and delightful to use. As a non-HR person, I find the intricacies of payroll, benefits, taxes, compliance, and expenses to be painful. So I just want something that makes my life easier. Second, I want it to be affordable.

I'm a bootstrapper at heart.

I started Morning Brew with $0 and I started StoryArc with $0 as well, which means I don't have infinite dollars to drop on SaaS products. And third, I want a platform that acts as my one-stop shop for all things people. I want it to handle payroll, benefits, hiring, onboarding, and taxes, all while integrating with all of the other tools in my business stack, whether it be QuickBooks, Slack, or Google Workspace? Well, Gusto hit the trifecta, which is why I am a customer and use it for every single one of my businesses. Yes, this is a paid sponsorship by the amazing team at Gusto, but I would sing their praises even if I wasn't being paid to do so. So if you're looking for a platform that takes the pain out of payroll benefits and HR, I highly recommend you check out Gusto. And if you sign up at gusto.com/alex, you will get your first 3 months free. Now onto the episode. What's up everyone?

This is Alex Lieberman and Founders Journal is back.

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Now let's get into it. I am back in the mud with one of my businesses, CTA, and I just spent half of my day sending cold LinkedIn DMs and responding to emails.

This, folks, is entrepreneurship.

This is the rule, not the exception, to what startup work looks like. It's important to call this out because entrepreneurship has started to take on the sexiness of a professional sport. Zuck is wearing gold chains and beating people to a pulp in jiu-jitsu. Bezos looks like he can bench press an Amazon truck. And like a professional athlete, people ooh and ahh at the life of an entrepreneur. The ability to build something huge, get publicly recognized, make a ton of money, and do what you want. But for all of the sexiness, what you don't see is the slog, the years of excruciatingly repetitive work that goes on as an entrepreneur works in private. You see Sara Blakely today, the self-made billionaire with a mansion in Atlanta. What you don't see is her cobbling together the first version of Spanx with her bare hands and going to Neiman Marcus every single day to move the rack to the front of the store. You see Brian Chesky running Airbnb. What you don't see is him selling Obama-themed cereal to keep the business alive and being rejected by 100 VCs on the path to raise money. You see me selling Morning Brew and working on new businesses. What you don't see is me placing thousands of flyers on Michigan's campus to scratch and claw for our first subscribers. You don't see losing 50% of our revenue overnight during COVID and considering taking donations so we didn't have to fire anyone. I love entrepreneurship. I'm so grateful for it, and it is unsexy and uninteresting most of the time. It is so important for aspiring entrepreneurs to be clear-eyed to that before they dive in, and it's so important for current entrepreneurs to remember that so they don't feel like they're the only one sitting in the muck. And that is why I want to spend this episode talking about boring work, the unsung hero of entrepreneurship. I'm going to talk about why I believe boring work is unavoidable, but I'm also going to talk about why I think founders spend too much time stuck in boring work. And finally, I'm going to share why boring work is a gift that you should be grateful for. Let's start with the first: boring work is unavoidable. I actually tweeted out about boring work the other day, and Mike Seguero, the CEO of ButcherBox, which is the $600 million a year meat subscription business, he said.

Why wouldn't you pay to outsource the stuff you find boring?

I'm sure there's an intern out there looking for a chance to learn from someone amazing. I agree that the mud of entrepreneurship is hard and underreported, but I also think too often founders do stuff they hate. Mike makes a good point, but I think in practice there are things that prevent this from being 100% possible, especially in the early days of business. Every business is resource constrained. Especially those that are bootstrapped, which is the typical way in which I build businesses personally. And whenever I bootstrap a business, my first constraint is time. I only have so much time in my day to work on each of my businesses while also filling the other buckets in my life, like my relationship with my wife, my health, et cetera, which means that any time I spend recruiting or training an intern is time not spent fighting to get revenue. Now, the classic argument to make here is that sure, there's a trade-off of time, but if bring on an intern and train them, I'll ultimately get way more time back once they are operating autonomously. But let's think about this practically. With my new business CTA, I have one full-time employee who is fully at capacity. Let's say we have enough revenue to cover our expenses for 3 to 4 months. Bringing revenue in the door is mission critical, and I would consider any time not spent on bringing revenue in the door as a misallocation of time. So all of that to say, the second that I have the luxury of putting time into an intern, let's just say that's 6 to 8 months of runway in the business, I will happily fire myself from the boring stuff. Let's talk more about being revenue constrained for a second. My goal with every one of my businesses right now is to fire myself within 6 to 12 months of starting the business. And the only way I can do that is to drive enough revenue to hire my replacement. But even when I hire my replacement, which I already have for CTA, it's not like I can just step out of the business immediately and leave my teammate hanging, which means 4 things need to exist before I can fully remove myself. The first is product. The second is process. The third is people. And the fourth is profit. I need to feel confident that we have product-market fit. I need to know that there's a repeatable process that will allow us to scale. I need to know my replacement will have the right people around them so they're not stuck in the mud constantly.

And I need to know that we have predictable revenue and we are profitable.

Which gets me back to boring work. Until your business is not human capital constrained or time constrained by you, you will be forced to do things that you do not enjoy. The alternative is the thing that you need to do just doesn't get done because you can't afford to hire someone to delegate to, or because you spend more time looking to automate, delegate or offshore the thing than doing it yourself. So that's the first point about boring work. I believe it is inevitable for months to years in business, depending on how time and money constrained you are with your specific business. The second thing about boring work, which is the flip side to my first point, is that I find many entrepreneurs, especially first-time founders, stay in boring work for far too long. Yes, I think that boring work is inevitable at first, but I also think you should avoid it at all costs. Boring work is typically low skill, low leverage, and typically a bad use of your time once you are not resource constrained. I find that tons of entrepreneurs spend too much time on boring work because they lack the awareness or the trust to give it up. And it's kind of a peculiar thing when you think about it. Boring work is boring. Why would anyone choose to do it? I don't think they actually do. I just don't think people see another option, even if they do have one. I was the most guilty of this in the early days of Morning Brew. I spent 2 to 3 years too long doing media sales at the Brew. This included LinkedIn DMing, email follow-ups, going on every sales call, and sending campaign reports to clients. As I reflect on that point in my startup career, I realize how much time I wasted. I could have delegated LinkedIn DMing to a sales assistant or a VA. I could have hired another junior seller to take sales calls. I could have given any campaign report work to an account manager. So why didn't I do any of this? Because I lacked trust and I lacked awareness. Let's talk about trust first. Trust has two sides. Belief in self and belief in others. I thought I was the world's greatest media seller, and I didn't think anyone could sell Morning Brew as well as me. Not only was I wrong, but I wasted tons of time where I could have been doing higher leverage tasks. I did boring work way past the point of it being an absolute necessity. The other part of this is awareness. In the early days of Morning Brew, I don't think I was aware how poorly I allocated my time and how much of it was spent on boring, low-value work. It reminds me of something that the founder of FanDuel told me a few years ago. When I spoke with him, he said he is currently running 3 different businesses, yet he has more free time than he ever did while running just FanDuel. I asked him why that is. He said, on FanDuel, I spent 80% of my time on the wrong things. On these 3 new businesses, I just spend my time on the right 20%. Now, obviously there's a bunch of low-value, boring work that Nigel from FanDuel couldn't have been aware of as he was running But I'm also sure that if he could go back with the right level of self-awareness, he could have brought that 80% wasted time number down. So what can you do to be self-aware of boring work? And how can you know when you've spent time on boring work for too long? It's actually quite simple. On a daily basis, you can just take a few minutes to reflect on how you spent your time in your business and ask yourself a simple question. What was the most productive thing I did today? What work did I do today that I didn't really love doing, and I am not uniquely qualified to do? Especially in the early days and early years of business, your answer to that question will include a lot of things. And then the next question you should ask yourself as you run down the list of work you didn't love and are not uniquely qualified to do is, am I doing this work because there is a time or cost constraint that prevents me from getting out of this work? Again, in the early days of your business, the answer will likely be yes. But as your business enters year 2, year 3, and year 4, and you are still able to list a lot of work that you don't love and you are not uniquely qualified to do, the answer to question 2 is likely no. No, there isn't a time or cash constraint preventing you from getting out of your boring work. It is likely just a lack of awareness, which these 2 questions provide for you, Or it is a lack of trust, which you need to push through if you ever want to build a business of scale where you aren't the bottleneck. The third and final way that I think about boring work is I believe it is a gift. It is a gift because it comes with the territory of being an entrepreneur. And while boring work is boring, it also affords you the ability to step back and be strategic about something that you own and control fully. And that is such a special thing, arguably the most beautiful part of entrepreneurship. You don't owe anyone anything. No one can tell you what you should do if you don't want them to. You are the author of your story, the captain of your journey, and if boring work is the price of that, I would say it is 1,000% worth it. But that's not the only reason it's a gift. Boring work is also a gift because it means you have the privilege of considering some work as boring and other work as non-boring. I can guarantee you that my parents or grandparents didn't have the luxury of considering the level of fulfillment of their job as they did it. I can also guarantee you that in the early days of Morning Brew, I wasn't thinking about whether some of my work was boring and some of it was exciting and fulfilling. I just had one goal: survive. And survival was the only need that occupied my brain for several years in my business. Boring work is a first-world work problem. Which means if you're thinking about it, you need to feel grateful that you have the choice to optimize how you spend your time on work versus just looking at work as a mechanism for survival. So just to recap, boring work is important to acknowledge at a time when entrepreneurs are celebritized and people aspire to be like their favorite entrepreneur. Entrepreneurship is great, but it also involves a lot of boring, thankless work to maybe have a chance at the type of success that you have observed publicly. I also believe that boring work is inevitable because of the scarce resources that define entrepreneurship. And yet the second that you are no longer constrained, I believe that you should do everything in your power to get out of boring work, something that many entrepreneurs, including myself, fail to do. And finally, I think boring work is a gift. It's a small sacrifice for the amazing opportunity that entrepreneurship affords all founders. And it is a great privilege as having the ability to think about boring work means that you're no longer thinking only about survival in your business. That is it for today's episode of Founders Journal. Thank you as always for listening to the podcast. Make sure to subscribe to the show if you haven't already done so, and also shoot me an email to alex@storyarb.com. That's alex@storyarb.com to introduce yourself and let me know what you'd like to see from Founders Journal moving forward. I love to get to know my listeners, so I will 100% reply if you send me a note. Thanks again, and I'll catch you next episode.